Nitrogen → 2-Acetyl-6-bromopyridine

HRID 42781Notes

Reaction equation

HRID 42781 reaction equation
N#N.Br[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[N:5]=1.[Li]CCCC.[NH4+].[Cl-].[CH3:18][CH2:19][O:20]CC>CCCCCC>[Br:10][C:6]1[N:5]=[C:4]([C:19](=[O:20])[CH3:18])[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 947NitrogenHCID 3283Diethyl EtherHCID 122742,6-DibromopyridineHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 112985782-Acetyl-6-bromopyridine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 2,6-dibromopyridine (2.44 g, 10.00 mmol) in ether (25.0 mL) was treated at −78° C. with n-BuLi (4.0 mL of a 2.5M solution in hexane, 10.00 mmol). The reaction mixture was stirred for 30 min before N,N-dimethylacetaminde (1.50 mL, 16.13 mmol) was added and the solution was then allowed to warm to rt over 1 h. Sat. aq. NH4Cl was then added and the aq. layer was extracted with Et2O (2×50 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (20:1 hept-EA) gave the title compound as a white solid: TLC:rf (20:1 hept-EA)=0.25. LC-MS-conditions 02: tR=0.98 min.

Workup

  1. additionwas added
  2. extractionthe aq. layer was extracted with Et2O (2×50 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (20:1 hept-EA)

Sources & evidence

ORD record
ord-74a1ee7139aa4f0db28213aa1bbf6c49
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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